Which of the following haloalkane is hydrolysed by SN1 mechanism?
Correct answer: D. (CH3)3CBr
- A. CH3Br
- B. CH3CH2Br
- C. CH3CH2CH2Br
- D. (CH3)3CBr
Explanation
SN1 reactions proceed through a carbocation, so the substrate that forms the most stable carbocation reacts most readily. (CH3)3CBr forms a tertiary carbocation stabilised by three methyl groups, whereas the methyl and primary bromides in the other options do not form stable carbocations. Students may choose a because methyl bromide is less crowded, but low steric hindrance favours SN2, not SN1.
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About Nucleophilic Substitution
Nucleophilic substitution replaces a leaving group in an alkyl halide when an electron-rich nucleophile attacks the carbon atom. The topic compares SN1 and SN2 mechanisms, including reaction conditions, substrate structure, solvent effects, nucleophile strength, carbocation formation and stereochemical changes, and distinguishes substitution from elimination.
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